Pharmaceutical Intermediates

(+)-Bicuculline, a light-sensitive competitive GABAA and GABAA-gated chloride channel antagonist, functions in the biochemical field as a drug, CNS stimulator, convulsant and neurotransmitter. Its chemical identities are alkaloid and phthalide-isoquinoline compound. Extracted from plant alkaloid in 1932, this metabolite has been definitively located in Adlumia fungosa, Dicentra cucullaria, Fumariaceae and some species of Corydalis. (+)-Bicuculline acts primarily on ionotropic GABAA receptors but also blocks Ca2+-activated potassium channels and can act as an agrochemical.

As a poisonous neurotoxin, it affects nervous system responses associated with GABAA by binding to the receptors but not activating them, thus inhibiting the action of gamma-aminobutyric acid. This produces a powerful convulsive reaction mimicking epilepsy and has been used in lab studies of the condition. Administered with NMDA, it has induced paraplegia. Injection to the amygdala has also produced GABA-related anxiolytic effects on emotional states.

1,2,3,4-Tetra-O-acetyl-β-D-glucuronic acid methyl ester has been used in various biochemical studies. It has been used to study the potential of water-soluble camptothecin glucuronide derivatives as a cancer prodrug monotherapy and antibody-directed enzyme prodrug therapy. Additionally, it has been used to assess the role of glycosylthio heterocycles in carbohydrates.

1,2-Benzoisothiazolin-3-one, sodium salt is an isothiazolinone biocine used in plants and as a preservative. Its mode of action is both fungicidal and microbicidal.

1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine or DPPE is a phospholipid component of the cell membrane. It is used in membrane models and is part of the glycerophosphoethanolamine family. DPPE has been shown to cause competitive hydrogen bonding of amine groups with phosphate/carbonyl groups or water. Additionally, DPPE has been studied along with cholesterol, showing cholesterol’s ability to induce DPPE monolayer condensation when calcium ions are present.

1,2-Octanediol has a variety of applications. It is used to improve HPLC separation of organic acids and bases and to synthesize halohydrin palmitates. Additionally, it is studied for its potential use as a pediculicide and has been shown to be effective against louse infestations.

1-O-Methyl-β-D-glucopyranoside is commonly used to study the specificity of yeast Saccharomyces cerevisiae in removing carbohydrates by fermentation. Additionally, it has been used to analyze alternansucrase acceptor reactions with methyl hexopyranosides.

2,2’-Bipyridine is a metalloprotease inhibitor used as a reagent for the colorimetric determination of iron. It is a base used for oxidation-reductions indicators and to confirm the presence of ferrous iron in soils. Additionally, 2,2’-bipyridine is used in transition metal catalysis and aluminum-initiated polymerization. It is a high-affinity iron chelator and may inhibit iron-containing enzymes.

2,4,6-Tris(2-pyridyl)-1,3,5-triazine or TPTZ is a triazine compound containing 3 pyridyl groups. It is commonly used as a reagent for the spectrophotometric determination of Fe(II) and total Fe. It can also be used to determine the amount of acetaminophen in samples through spectrophotometry.

2-Deoxy-D-galactose is a deoxy hexose that inhibits synthesis of glycoproteins in Influenza virus, such as hemagglutinin and neuraminidase, by blocking glycosylation. 2-Deoxy-D-galactose also inhibits the glycosylation of mammalian proteins involved in neurotransmitter release and synaptogenesis in the hippocampus. It has been used for isolating galactose permease mutants of Salmonella typhimurium and in the inhibition of glycolysis in Saccharomyces cerevisiae. It has also been used to isolate and elucidate the activity of a system for galactose uptake into E. coli.

2-Nitrophenyl-β-D-galactopyranoside or ONPG is a chromogenic substrate for β-galactosidase. Upon hydrolysis, ONPG releases galactose along with a chromogenic yellow compound. Additionally, ONPG is a substrate useful for the determination of β-glucosidases.

3-Indoxyl-3-acetate is a chromogenic substrate used to differentiate between esterases of various microorganism species.

4-Benzyloxyindole is a reactant in a variety of preparation procedures. It is used in the synthesis of 4-aryl-4H-chromenes as an inducer of apoptosis, in the synthesis of indol-3-yl tetramethylcyclopropyl ketones as a CB2 cannabinoid receptor ligand, and in the synthesis of hepatitis C inhibitors. Additionally, 4-Benzyloxyindole is used to prepare carbon-11-labeled-4-aryl-4H-chromenes as PET agents in cancer studies, to prepare indoles through Bartoli reductive cyclization, and to synthesize oxopyrrolidine analogs in iodine-catalyzed Markovnikov additions.

4-Bromoindole is studied for its potential use as a GSK-3 inhibitor.

4-Methoxyindole is used in a variety of preparation procedures. It is a reactant involved in the synthesis of GABA analogs, HIV-1 integrase inhibitors, anticancer agents, sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors, integrase strand-transfer inhibitors (INSTIs), and isomeridianin G. Additionally, it is used in reverse-phase liquid chromatography analysis of the reaction of β-cyclodextrin and pindolol.

4-Methylumbelliferone is useful as an indicator in the determination of nitric acid. It is also useful in the kinetic investigation of enzyme activity. 4-Methylumbelliferone is fluorescent in alkaline solution.

4-Methylumbelliferyl alpha-L-idopyranosiduronic acid sodium salt is a carbohydrate acid and organic sodium salt applied as an indicator. It is the fluorogenic substrate used in assays of α-L-Iduronidase and iduronate-2-sulfatase for identifying Hurler syndrome, also called mucopolysaccharidosis type I (MPS I). The disorder is characterized by α -L iduronidase enzyme deficiency, resulting in the buildup of glucosaminoglycans. Tests measure the chemical products 4-MU-α-IdoA or fluorophate 4-MU emitted following the enzymatic action of 4-Methylumbelliferyl alpha-L-idopyranosiduronic acid sodium salt. The substance is a white crystalline powder and is soluble in ethanol, methanol and water.

4-Nitroindole is used in the synthesis of a variety of compounds including: indoles, nucleosides, CB2 cannabinoid receptor ligands, CGRP receptor antagonists, anti-angiogenic agents, meridianin derivatives, tryptophan dioxygenase inhibitors, and 1,3,4,5-tetrahydropyrrolo-[4,3,2-de]quinoline.

5-Amino-2-nitrobenzoic acid is a reagent used in preparation of polymer-bound diazonium salts and insulin receptor tyrosine kinase activator. It is also used in 2-component dendritic chain reactions and activation of hydrophobic dendrimers.

5-Aminoindole is used in a variety of preparation applications. It is used to prepare cytotoxic and antimitotic agents, HIV protease inhibitors, PCKθ inhibitors, IGF-1 receptor inhibitors, anticancer agents, antivascular agents, tyrosine kinase receptor inhibitors, and Smac mimetics binding the XIAP apoptosis-inhibiting protein.